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Phenol
pKa = 9-11
Acidic under physiological conditions

Sulfonamide
pKa = 9-10
Acidic under physiological conditions

Imide
pKa = 9-10
Acidic under physiological conditions

Alkylthiol
pKa = 10-11
Acidic under physiological conditions

Thiophenol
pKa = 6-7
Acidic under physiological conditions

N-Arylsulfonamide
pKa = 6-7
Acidic under physiological conditions

(N-)Acylsulfonamide
pKa = 5-6
Acidic under physiological conditions

Alkylcarboxylic Acid
pKa = 5-6
Acidic under physiological conditions

Arylcarboxylic Acid
pKa = 4-5
Acidic under physiological conditions

Sulfonic Acid
pKa = 0-1
Acidic under physiological conditions

Imine
pKa =3-4
Basic under physiological conditions

Arylamine
pKa = 4-5
Basic under physiological conditions

Pyridines
pKa = 5-6
Basic under physiological conditions

Alkylamines
pKa = 9-10 (primary), 10-11 (secondary)
Basic under physiological conditions

Amidine
pKa = 10-11
Basic under physiological conditions

Guanidine
pKa = 12-13
Basic under physiological conditions

Alkyl Alcohol
pKa =
__ under physiological conditions

Ether
Neutral

Ester
Neutral

Sulfonate Ester
Neutral

Amide
Neutral

Thioether
Neutral

Aldehyde
Neutral

Sulfoxide
Neutral

Nitrile
Neutral

Diarylamine
Neutral

Ketone
Neutral

Sulfone
Neutral

Carbamate
Neutral

Amine Oxide
Permanently charged across pH range

Quaternary ammonium
Permanently charged across pH range
